The macrolide leiodermatolide was isolated from the marine sponge Leiodermatium sp. and exhibits strong antiproliferative activity against a range of cancer cell lines via an unknown and potentially novel mode of action. In order to fully elucidate the structure and provide a sustainable supply of synthetic material and modified analogues for biological studies, a highly stereocontrolled and convergent synthesis has been developed. This utilises highly efficient boron mediated anti aldol methodology developed in our group to set up the majority of the stereocentres with excellent stereoselectivity. A series of palladium mediated cross couplings are then used to connect the key fragments and form the five double bonds in a geometric controlled manner en route to completing the synthesis of leiodermatolide.

Total synthesis of leiodermatolide

249th National Meeting (2015)

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